


Trying Something New

by Oumasaikomahinanaegamitokomaruirumatsu



Series: Saiouma 30 Day otp challenge [3]
Category: Dangan Ronpa - All Media Types, New Dangan Ronpa V3: Everyone's New Semester of Killing
Genre: Anal Sex, Bottom Saihara Shuichi, Bribery, Cash Reward, First Time, Large Cock, Loss of Virginity, M/M, Making Love, Making Out, Rough Sex, Sex, Top Oma Kokichi, Trans Saihara Shuichi, Vaginal Fingering
Language: English
Status: Completed
Published: 2021-01-18
Updated: 2021-01-18
Packaged: 2021-03-16 04:01:55
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,878
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28824897
Author URL: https://archiveofourown.org/users/Oumasaikomahinanaegamitokomaruirumatsu/pseuds/Oumasaikomahinanaegamitokomaruirumatsu
Summary: Miu bribes Kaito, Maki, Kaede, and Shuichi, who are all virgins, a cash reward to who can lose their virginity first. Shuichi isn't sure what to do, let alone if he wants the money, but Kokichi comes around and says he can help Shuichi.
Relationships: Oma Kokichi/Saihara Shuichi
Series: Saiouma 30 Day otp challenge [3]
Series URL: https://archiveofourown.org/series/2090364
Comments: 6
Kudos: 77





	Trying Something New

**Author's Note:**

> Hi everyone. My brain is shifting from thinking, so I might be writing more Binder Shuichi if that's okay. I'm sorry, my brain likes to shift from concept to concept sometimes. I will definitely write Top Surgery Shuichi when I have the motivation to.
> 
> Prompt: First Time

“Alright you fuckers!” Miu yelled out to Kaede, Kaito, Maki, and Shuichi, who were gathered around her. “How does that sound?!”

The four of them exchange glances. Miu won $1000 dollars in a lottery and offered to give $500 to whoever could lose their virginity first. 

“Well, I’ll leave you to think!” Miu got up from where she was sitting. “Also, ya can’t ask me to help fuckers!” Miu laughed as she walked away. 

“If we have sex with each other” Kaito began. “We can all get the money, right? I’ll take Maki Roll and Shuichi can have Kaede.”

Maki sighed. “I-If it works for all of you. If someone disagrees, I won’t do it with you.”

“What do you think, Shuichi?” Kaede turned to him. “Does that sound like a good plan?”

“I-I don’t know.” Shuichi said, flustered. “This is happening too fast. I-I need time to think.”

“Take as much time as you need!” Kaede chirped happily. “There’s no time limit!”

Shuichi went outside to the courtyard of the school to think. He sighed, not knowing what to do. He’s never even touched himself before. 

“Boo hoo hoo” Kokichi began to pout, coming closer to Shuichi. “Shuichi’s so upset! You gonna cry? Are you? Are you? Hey!” 

“Not now, Kokichi.” Shuichi sighed. “I’m thinking.”

“Is it about what Miu said?”

“H-How did you know?!”

“Duh! I heard her loud ass screaming that she won a lottery! Then she made that craaazy invention that sees if you’re a virgin. I guess she targeted the four of you since you were all friends, and virgins!”

“A-Are you not a virgin, Kokichi?” Shuichi looked at him. Kokichi shook his head. “I turned a homophobe at my school to a homosexual, babe.”

Shuichi blushed at what Kokichi said. 

“You want me to help you?” Kokichi asked Shuichi, who began to get flustered at the question. “I-I don’t even know if I want the money.” Shuichi said. “Detective work is well paid, so I wouldn’t really need it.”

“It's good to have the extra cash though.” Kokichi’s hands sneaked their way behind Shuichi to pull the detective closer. “Don’t you wanna do it with someone skilled? Come on, pweeeeasee? It’s so mean to deny a sex request!”

Shuichi sighed. ‘Kokichi would know what he is doing. How bad could it be?’

“I’ll do it.” Shuichi sighed. “Not because I want the money, it's because I want to do it with you.”

“Really?” Kokichi smirked. He picked up Shuichi bridal style. “Great! Off to my Ultimate Lab!”

Kokichi carried Shuichi to the underground area, known as the lab of the Ultimate Supreme Leader. 

“Since you are in my lab…” Kokichi began speaking as he set Shuichi down on the ground. “You are to listen to me. I am your leader, and I am in control over you. You are mere property to me here. I own you, and you will do as I say, or else. Do I make myself clear?”

“Y-Yes sir.” Shuichi spoke nervously, not wanting to fall out of line. 

“Good boy.” Kokichi said, kneeling down to Shuichi. “Usually, people start with preparations for sex. I shall prepare you for what's about to come. Pun intended.” Shuichi didn’t understand the joke. 

“You are going to let me passionately kiss you. Do you understand?” Kokichi grabbed Shuichi’s face, pressing his cheeks together to pucker his lips. Shuichi nodded. 

Kokichi pressed his lips against Shuichi’s. He pulled the bluenette closer to him. A few seconds later, he slipped his tongue into Shuichi’s mouth. Shuichi also moved his tongue, and the two tongues danced in a fight for dominance. Kokichi tasted of Grape Panta, which was no surprise to Shuichi. Kokichi then pulled away, giving Shuichi some time to catch his breath. 

“Aah, that felt good.” Kokichi sighed. “You tasted so sweet baby~ Now I must mark you. You will give me access to your neck now. Understood?”

“Yes sir.” Shuichi removed his black jacket, leaving him in his white button up shirt. This also revealed his neck. Kokichi got on top of Shuichi and began to lick his neck. Shuichi let out moans. He tried to cover his mouth, but Kokichi pulled his hand away. 

“Non non, my beloved.” Kokichi said, still licking. “I wanna hear those sounds.”

Shuichi moaned loudly as Kokichi began to bite and suck on Shuichi’s neck. Kokichi then stopped, leaving a bruise-like mark on Shuichi’s neck. 

“That’s called a hickey, beautiful.” Kokichi began to remove his scarf and his dice jacket. “Shows that you’re mine. Now come on, remove the shirt.” 

“I-I don’t know…” Shuichi was nervous. He was worried that Kokichi wouldn’t want to do it anymore. “Are you disobeying my orders?” Kokichi growled. “Listen bitch. You’re mine. You do as I say. Got that, you whore?”

“Y-Yes s-sir!” Shuichi quickly removed his button up shirt, revealing his black binder. 

“I suggest taking off your binder for this kitten~” Kokichi cooed, throwing Shuichi’s shirt aside. “It’s healthier. I won’t touch your tits if you don’t want me to~”

“I-It’s okay.” Shuichi removed his binder, revealing his average sized breasts to Kokichi. “I’m your property. You own me. Please, do as you wish with me.”

Kokichi smirked, looking at the helpless trembling detective. “Good boy~ So quick to understand his place. Oh so good~” Kokichi buried his face into Shuichi’s cleavage, which made Shuichi gasp out in surprise. 

“Gah!” Shuichi squealed out in surprise. “K-Kokichi!” Kokichi looked up and squished Shuichi’s breasts to his face. A“Ready to feel good babe?~” Kokichi asked, a husky voice arising from him. Shuichi nodded shyly, not knowing what was coming for him. 

Kokichi took Shuichi’s left breast into his mouth and started sucking on it. He took the detective’s right breast and squeezed it roughly. Shuichi let out more melodious moans of pleasure.

After a couple of minutes, Kokichi switched breasts. Now he was sucking on Shuichi’s left boob and he was squeezing his right one roughly. Shuichi let out more moans and whines. 

After biting down once on Shuichi’s nipple, Kokichi removed his mouth and hand from Shuichi’s breasts. “Your pants and underwear.” Kokichi said to Shuichi sternly. “Take them off.” Shuichi removed the remainder of his clothes. 

“Ooh, so pretty~” Kokichi growled low. “Spread your pretty little legs wiiide open for your leader kitten~” “Y-Yes sir!” Shuichi spread his legs as far as he could. Kokichi got in between his legs and gave his pussy a few good licks.

“Aah~” Shuichi moaned. “Th-This feels weird!~”

“That’s cuz it’s new to you baby~” Kokichi said as he forced his tongue inside Shuichi’s clit. Shuichi let out moans of pleasure, his clit getting tight around Kokichi’s tongue. Kokichi began to growl against Shuichi’s walls, making him quiver. He soon let out a loud moan as he came. Kokichi took some of Shuichi’s cum onto his finger. 

“This white liquid on my finger.” Kokichi began to educate Shuichi. “It’s called cum.” Kokichi licked Shuichi’s cum off of his finger. “You’re gonna swallow mine up, and you’re gonna take it all. Understand?”

“Y-Yes sir~ Please, please let me taste you~” Shuichi was practically hypnotized. 

“Oh?” Kokichi began to remove the rest of his clothes. “Is someone needy for my cock and cum? Does someone want me to cum in their mouth?” 

“Y-Yes!” Shuichi moaned. “P-Please! Wh-What do I need to do to get it from you?~” 

“Put your mouth over my cock.” Kokichi forced Shuichi’s mouth on his cock. He pushed the detective all the way to his ballsack, making the detective gag. “Move your mouth up and down. Go on. Start. Now.”

Shuichi moved his mouth over Kokichi’s cock, making Kokichi grunt. “Good boy.” Kokichi grunted. “Oh yes oh yes such a good boy~ Haah~ Yes that’s right you slut~ You whore bitch~ Move that little mouth of you’RS oh god I’m close. I’m gonna- AAH~”

Kokichi came after a couple minutes, and Shuichi swallowed all of it. “Such a good boy…” Kokichi panted heavily. “Oh you took it like a champ~ So good for your first time~ Now stick your ass up so I can prepare you for when I enter~” 

Shuichi did as he was told, sticking his ass in the air. His big, juicy, scrumptious behind looked like a prize to Kokichi. The leader put some lube on his fingers and stuck one finger in. Shuichi moaned loudly as Kokichi swirled his finger around. He stuck another finger in, scissoring the poor boy’s hole. “Aah~ Sir~ I-It feels so good- AAH~ TH-THERE~” Shuichi moaned loudly as that spot that made him crazy was hit.

“Aah, so THAT’S where you’re hiding~” Kokichi snickered as he pushed a third finger in and abused that spot, making Shuichi moan like crazy. Kokichi went at it for a while, until Shuichi screamed as he came. 

“I love those sounds~” Kokichi cooed. He stood up and lined himself up with Shuichi’s hole. “Now we get to move on to the real fun! Are you ready for Sir’s big cock to absolutely wreck you~ Are you ready to hand your sweet little virginity to lil ol me~”

“Yes yes oh yes~” Shuichi whined needily. “Sir please enter me~ I want you~ I want you so badly~”

“Okaaaay!” Kokichi cooed enthusiastically. “Here we gooooooo!” Kokichi shoved his cock into Shuichi, who let out a scream of both pain and pleasure. Kokichi pushed in slowly, stroking Shuichi’s face as he pushed in slowly.

“Okay sweetheart~” Kokichi grunted. “I’m all the way in, let me know when you want me to move~”

“Y-You can move, sir~” Shuichi moaned. “Wreck me. Wreck me good. I want you~” 

“What a good little slut~” Kokichi began to move, Shuichi began to moan and scream. “Aah!~ Ooh! Mmh!~ So good!~ So good sir!~ Faster!~ Harder!~ More!~” 

“That’s right bitch.” Kokichi growled and grunted. “That’s right you slutty whore bitch. Who’s your sir? Say it. Say it you whore bitch! Fucking tell me!”

Shuichi was crying full of pain and pleasure. “Y-You are!~ You’re my sir!~ You’re my sweet, strong sir!~ I’m nothing but you’re property!~ Property for you to fuck forever!~”

“That’s right.” Kokichi growled. “You’re my property. Mine. Now, cum for me whore.

“K-KOKICHI~” Shuichi screamed as he came. “Sh-ShumAI~” Kokichi moaned out, cumming a few thrusts after. Kokichi pulled out, and both boys were panting. 

“Howzit feel?” Kokichi panted heavily. “Howzit feel… to not be a virgin anymore Pookie?” Silence. “Pookie?” Kokichi looked over to see Shuichi passed out, sleeping soundly like a baby. “Tiring, ain’t it Tutz?” “Rest up Pookie. You deserve it. You took it like a champ and did so well~”

The Next Morning…  
“Woah!” Miu chirped, loudly and excitedly. “Shuichi isn’t a virgin anymore!”

“What?!” Kaito, Maki, and Kaede yelped out in shock. 

“You guys can have the money!” Shuichi said. “I’m sorry, I couldn’t help myself. I wanted to stop, I really did, but it felt so good.”

“Glad you enjoyed it Shumai!” Kokichi smirked and kissed Shuichi on the cheek. “Let’s do it again sometime~” Kokichi left the cafetiera, as Shuichi sighed. “He’s so good with his cock~”

Miu bursts out laughing, which caught Shuichi’s attention. Kaito, Maki, and Kaede looked at him. Shuichi Saihara had a lot of explaining to do.

**Author's Note:**

> Thanks for reading! Lmk if yall have any requests! :D


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